Weekend & second-home buyers
The town line decides your weekend home, not the house
What NYC buyers looking at Woodstock, Rhinebeck and Stone Ridge should check before they fall in love.
By Ryan Rooney
Every spring I get the same call. Someone in Brooklyn or on the Upper West Side has been coming up for weekends, has stayed in the same rental three or four times, and has decided this is the year. They send me a Zillow link. Usually a farmhouse with good bones, in a town they've visited twice.
The house is almost never the problem. The town is.
In Ulster and Dutchess, two houses that look identical online can sit four miles apart and live under completely different rules, prices, and travel math. The buyers who find that out after they're under contract are the ones who end up unhappy about it. So here's what I walk people through before they tour anything, in the order it actually matters.
1. The price spread between towns is wider than the listings suggest
Ulster County overall is a mid-four-hundreds market. Over the three months ending June 2026, the county's median sale price was about $450,000, up roughly 3% year over year, with a median of 39 days on market. More than 43% of homes sold above asking.
That county number is close to useless if you're buying a weekend house, because you're not shopping the county. You're shopping about six towns, and those towns run well above the median:
- Woodstock came in around a $780,000 median, up about 7% year over year, selling in roughly 40 days.
- Stone Ridge ran around $612,000.
- Rhinebeck, across the river in Dutchess, was closer to $950,000.
Two cautions on those town figures, because I'd rather you trust me in month six than be impressed in month one.
These are small towns. A quarter's worth of sales in Stone Ridge or Rhinebeck can be four transactions, and one big sale swings the median hard. Treat the year-over-year percentages in small towns as noise, not trend. And these are portal numbers. Before you write an offer, I'd pull the actual closed comps out of the MLS for the road you're buying on, because around here the difference between a ridge with a view and the parcel below it is real money.
The practical version: the gap between a Woodstock budget and a Saugerties or Marlboro budget isn't 10%. On a similar house it can be a third of your purchase price, and a lot of that premium buys the town's name rather than the building.
2. Whether you can ever rent it out was decided before you showed up
This is the one that costs people money, and almost nobody raises it until the deal is done.
Plenty of weekend buyers plan to offset the carrying cost by renting the place when they're not in it. Even just a handful of weekends. In this region that plan lives or dies on a town-by-town short-term rental law, and the towns most people want are the towns that already closed the door.
Roughly where things stand this summer:
- Rhinebeck is among the tightest in the region, on both sides of the town and village line. The village runs a permit application through Village Hall. The town has been reworking its own law. Don't assume anything here without calling first.
- Town of Woodstock operates under a cap. Published summaries disagree on the exact number, but what gets reported to me is that new slots open mainly when an existing permit lapses.
- Town of Marbletown, which contains Stone Ridge, allows a limited number per owner, with an annual permit and inspection.
- City of Kingston capped whole-home short-term rentals at 1% of the city's housing units, which worked out to 106 permits. It's been full since early 2024, and the city's own fact sheet says whole-home permit requests are rejected until further notice. Resident-occupied and limited permits, under 30 nights a year, are a separate category and aren't capped the same way.
- Town of Saugerties is, in my read, the most workable law in Ulster County right now. Annual permit and safety inspection, no cap currently enacted, no owner-occupancy requirement. It applies to single-family homes and permitted accessory apartments, though, not two-family or multi-family.
- Town of Ulster and a few smaller towns still had no dedicated short-term rental law as of mid-2026.
Three things I tell every buyer about that list.
A permit process existing is not the same as a permit being available. Ask the code enforcement officer how many are open today, and get the answer in writing.
In several towns the permit doesn't transfer when the property sells. The seller's five-star Airbnb history tells you nothing about your own rights.
And villages and towns overlap constantly here, so check the tax map, not the mailing address. A Rhinebeck mailing address doesn't tell you whether you're inside the village.
Treat every bullet above as a starting point rather than a final answer. The published summaries of these laws contradict each other regularly, and towns amend them. I confirm with the town before a client relies on it, and you should expect your agent to do the same.
The long version, covering 38 municipalities with the source shown for each one, is in my short-term rental permit guide.
3. How you'll actually get here in February
Everyone tours in October, when the drive up the Thruway is beautiful. Decide based on the trip you'll make forty times a year, in the dark, in weather.
If you're driving from the city, the towns west of the river run roughly two hours from Manhattan, longer on a Friday, and the last twenty minutes is often a winding secondary road that gets meaningfully harder in snow. Ask about the road, not just the town. Is it town-maintained or private, and who plows it.
If you want to arrive without a car, that means the east side of the river or something close to a station. Amtrak runs Penn Station to Rhinecliff in about an hour and forty minutes, roughly hourly, which puts Rhinebeck and Red Hook genuinely in reach for a Friday evening arrival. And since October 2025, Metro-North has run super-express Hudson Line trips covering Poughkeepsie to Grand Central in under 90 minutes. There are six a day, three out of Poughkeepsie in the morning and three out of Grand Central later, so they're useful if your schedule bends and irrelevant if it doesn't. Standard service on that stretch can run up to about 115 minutes.
That train access is a big part of why Rhinebeck prices where it does, and why a comparable house forty minutes west costs materially less. You're not overpaying for Rhinebeck. You're paying for the train.
What I'd do in your position
Pick the constraint first, then shop.
If renting it out is essential to the math, start from the towns where a permit is actually available and work backward to houses. If arriving by train is essential, start from the stations. If neither one is essential, the whole county is open to you, and you should be looking at the towns nobody has written a magazine article about yet. That's where the money goes furthest.
And come see it in the winter before you commit. The Hudson Valley in October sells itself. February is the honest version.
One more thing worth knowing
A meaningful share of the houses that fit this profile trade before they ever reach the public portals. Coming-soon and pre-market inventory in Ulster and Dutchess skews toward exactly the price band and property type weekend buyers want, which means anyone watching Zillow alerts is consistently seeing what's left over.
I track that inventory daily across both counties. If you're shopping for a weekend or second home up here and want to see what's coming before it's listed, message me with the towns you're considering and a rough budget and I'll add you to the list.
Ryan Rooney is a Licensed Real Estate Salesperson with Stevens Real Estate at eXp Realty, serving Ulster County and Dutchess County, New York. Born and raised in New Paltz. (845) 447-9274 · rrooney@stevensre.com
Market figures reflect Redfin data for the three-month period ending June 2026. Rail times reflect published Amtrak and Metro-North schedules. Short-term rental rules change frequently. Confirm current requirements with the individual town before relying on them.